2-Amino-5-bromopyridine → Ethyl [(5-bromopyridin-2-yl)carbamothioyl]carbamate

HRID 1844446Notes

Reaction equation

HRID 1844446 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:9]([O:11][C:12]([N:14]=[C:15]=[S:16])=[O:13])[CH3:10]>O1CCOCC1>[CH2:9]([O:11][C:12]([NH:14][C:15]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[S:16])=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 85320Ethyl isothiocyanatoformate

Product 1

HCID 59286274Ethyl [(5-bromopyridin-2-yl)carbamothioyl]carbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5-bromopyridin-2-amine (14.7 g, 85.0 mmol) and ethoxycarbonyl isothiocyanate (11.1 g, 10.0 ml, 85.0 mmol) in dioxane (300 ml) was stirred for 18 hours at 25° C. under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the solid yellow residue was diluted with ethyl acetate and washed with water and brine, the organic layer was separated, dried over magnesium sulfate, filtrated and evaporated to dryness. 26.2 g (quant.) light yellow solid. Mp.: 159-161° C. MS: m/z=304.0/305.9 (M+H+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe solid yellow residue was diluted with ethyl acetate
  3. washwashed with water and brine
  4. customthe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0f9ad79cecde4d8b933f4d4f6120a5fa
Source dataset
uspto-grants-2015_02
Patent number
US08946427B2

Reaction notes

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